CA1245669A

CA1245669A - Process for synthesizing alkyl monoperoxysuccinic acid bleaching compositions

Info

Publication number: CA1245669A
Application number: CA000485558A
Authority: CA
Inventors: Hao Ku
Original assignee: Clorox Co
Current assignee: Clorox Co
Priority date: 1984-07-02
Filing date: 1985-06-27
Publication date: 1988-11-29
Also published as: AU4421785A; EG17195A; EP0168204A2; TR24959A; US4659519A; ES8802073A1; MX165386B; DE3570871D1; ES545226A0; EP0168204B1; ES552817A0; ES8703416A1; AU592758B2; EP0168204A3

Abstract

ABSTRACT OF THE INVENTION

The invention relates to novel surface active peroxyacid bleaching agents and compositions which are named .alpha. or .beta. alkyl monoperoxysuccinic acids and have the general structure wherein R is an unsubstituted or substituted straight chain alkyl of 6 to 16 carbon atoms, unsubstituted or substituted branched chain alkyl of 6 to 20 carbon atoms, or a phenyl group substituted with one or more of H, alkyl of 1 to 14 carbon atoms, F, Cl, NO3, OSO3M, SO3M, or COOM, and M is further defined as H, an alkali metal or ammonium cation.

The invention also provides a novel process for synthesizing these alkyl monoperoxysuccinic acids which is relatively inexpensive, high yielding, and safe.

The bleaching compositions are useful for bleaching fabrics and other laundering purposes. The bleaching compositions of the invention may also contain peroxyacid stabilizers, builders, fillers, and surfactants.

Description

~5~6~
DESCRIPTION

ALKYL MONOPEROXYSUCCINIC ACID BLEACHING COMPOSITIONS
AND PROCESS FOR SYNTHESIZING THEREFOR

Technical Field __ I

The invention relates to surface active peroxyacids which are useful as bleaching compositions.

Background of the Invention Recently, manufacturers have been developing peroxyacid (also denoted as "peracid") bleaching agents. Efforts have been made to lQ identify and obtain further peroxyacid bleaching agents which can effectively oxidize stains.

Summary of the Invention This invention provides novel surface active peroxyacid bleaching agents comprising peroxyacids of the general structure:

O
Il !
~ - C - O - OH f, H HC - C - OH

wherein R is a substituted or unsubstituted straight chain alkyl of 6 to 16 carbon atoms, substituted or unsubstituted branched chain alkyl of 6 to 20 carbon atoms, or a phenyl group 20 which is substituted with one or more of H, alkyl of 1 to 14 carbon atoms, F, Cl, NO3, OSO3M, SO3M, or COOM, and wherein M is further defined as H, an alkali metal or ammonium cation.

~$66~

These particular compounds may also be called CYor ~ - alkyl monoperoxysuccinic acids.

The invention further provides a bleaching composition comprising the above peroxyacid in combination with a stabilizer selected from hydrated aluminum salts, hydrated magnesium salts, carboxylic acids and boric acid. Bleaching compositions of this sort can also contain fillers, builders, and surfactants.

The invention still further provides a method of bleaching fabrics comprising contacting fabrics with the foregoing bleaching compositions The invention also provides a novel process for preparing these CYor ~ alkyl monoperoxysuccinic acids comprising:

(a) combining:
( i) an alkyl succinic anhydride;
( ii) a water immiscible solvent;
(iii) a water soluble solvent; and ( iv) hydrogen peroxide; and (b) agitating under heat.

The invention thus provides both novel peroxyacid compositions 20 and a new, relatively inexpensive, high yielding, safe process for producing these compositions.

Brief Description of_the Drawings I
Fig. 1 is a graphical depiction of the decay kinetics of octyl monoperoxysuccinic acid and octyl butane diperoxic acid.

-2-~2~ 6~

Fig. 2 is a graphical depiction of the decay kinetics of decyl monoperoxysuccinic acid and decyl butane diperoxic acid.

Fig. 3 is a graphical depiction of the decay kinetics of dodecyl monoperoxysuccinic acid and dodecyl bu-tane diperoxic acid.

Detailed Deseription of the Invention It has been surprisingly discovered that ~ or ~ alkyl monoperoxysuceinie acids and their derivatives are effective bleaehing agents. These particular eompounds had not been heretofore synthesized. These novel bleaehing agents have now been prepared, and the proeess of synthesizing them is diselosed as set forth below.

~4~i~5~
CYOR ~ ALKYL MONOPEROXYSVCCINIC ACIDS

These surface active alkyl monoperoxysuccinic acid bleaching agents have the general structure:

o R ~ C - O - OH
H HC - C - O~

-..5 ~.~

wherein R, is a substituted or unsubstituted straight chain alkyl of 6 to 16 carbon atoms, substituted or unsubstituted branched chain alkyl of 6 to 20 carbon atoms, or a phenyl group which is substituted with one or more of H, alkyl of 1 to 14 carbon atoms, F, Cl, NO3, OSO3M, SO3M, or COOM, and wherein M is further defined as H, an alkali metal or ammonium cation.

Particular examples of the straight chain CY or~ alkyl - monoperoxysuccinic acids which have been synthesized include the octyl, decyl, and dodecyl monoperoxysuccinic acids, whose structures are set forth below:

CH3-(CH2)7 ~ -C-O-OH
H C-C-OH
Il CY or ~-octylmonoperoxysuccinic acid 5~

CH3-(CH2)g ~ C~O~OH
H HC-C-OH
o CYor ~ -decvlmonoperoxysuccinic acid ~ ~`' - .`
o CH3-(C~2)1 ~ -C-O-OH
H C 0~

CY or ~ -dodecYlmonoperoxysuccinic acid ~ .

PROCESS FOR SYNTHESIZING

Substituted, non-surface active peroxyacids (also denoted as peracids~ have been synthesized by combining a source of hydrogen 10 peroxide with an anhydride in the presence of an organic, polar solvent, such as ~ethylene chloride. See, S.N. Lewîs, ~Peracid and Peroxide Oxidations,~ Oxidation, Volume 1, p. 217 (1969).
These systems do not experience the problems that are encountered when one tries to make surface active peracids.
1, Other systems at present which vary the standard process include, for example, Camden et al, U.S~ Patent 4,233,235, which discloses a continuous process for making aliphatic diperoxyacids in thich a strong acld, sul~uric a id is added to an aliphatic ~56Ç~3 carboxylic acid mixture. Unfortunately, this particular system appears to generate large amounts of heat" and to require relatively expensive processing eyuipment.

Still other references have proposed other types of solvents.
5 However, none of the references appeared to have disclosed how to synthesize surface active monoperoxysuccinic acids. Further, nothing in the prior art discloses a process for making relatively pure surface active monoperoxysuccinic acids.

The surface active monoperoxysuccinic acids of this invention 10 are believed to be advantageous over other peroxy acids, for instance, the alkyl butane diperoxoic acids, which are somewhat similar compounds, but which have two peroxo moieties.
As disclosed herein, the novel process comprises:
(a) combining:
(i) an alkyl succinic anhydride;
(ii) a water immiscible solvent;
tiii) a water soluble solvent; and (iv) hydrogen peroxide; and (b) agitating under heat.

The alkyl succinic anhydride starting materials of the inventive process have the general structure:

O
'~
t ~o~
. ,.-,"
~Le ~ !

.

~15~
wherein R is an alkyl group of 6 to 20 carbon atoms.

The R group on these anilydrides may be appropriately substi~uted, as defined above, for surface active alkyl monoperoxysuccinic acid, to include br~nched chain alkyls, water solubilizing groups, e.g., S03H, etc., so as to form the peroxyacids discussed and depicted herein above.
The water immiscible solvents used herein include halogenated, i~e., chlorinated, fluorinated or chlorofluorinated alkyls of 1 to carbon atoms and unsubstituted and halogenated aromatic o hydrocarbons of 6 to 12 carbon atoms.

Representative halogenated alkyls include methylene chloride (dichloromethane) and carbon tetrachloride (tetrachlorornethane).
Representative aromatic hydrocarbons include toluene, dichlorobenzene, etc. Methylene chloride is especially preferred l5 as the water immiscible solvent.

The water soluble solvent used herein includes straight chain, branched chain, and substituted alcohols oE 1 to 6 carbon atoms;
straight chain, branched chain and substituted glycols of 1 to 6 carbon atoms, and straight chain, branched chain, and substituted 20 glycol ethers of 1 to 6 carbon atoms. Still other candidates include esters of 1 to 10 carbon atoms and ketones of 1 to 6 carbon atoms. Yet other possible solvents include such diverse solvents as dioxane, acetonitrile, dimethylformamide (DMF) and tetrahydrofuran (THF).

Synthesis of the desired monoperoxysuccinic acids require water soluble solvents. In practice, it has been discovered that these solvents carry the hydrogen peroxide into the nonaqueous phase of the alkylsuccinic anhydride/immiscible solvent ~ixture.

~2~ 9 The pre~erred water soluble solvent is an alcohol of 1 to 6 carbon atoms. One particularly preferred alco~lol is ethyl alcohol or ethanol.

It is preferable that neither the water immiscible solvent nor the water soluble solvent react with either the peroxyacid or H202 in situ. The apparent preference for such selectively non-reactive solvents is based on preventing an early decomposition of the peroxy compound formed in the reaction medium.

Eurther, the preferred volume ratios of the water immiscible 10 solvent to water soluble solvent is at least 2:1, more preferably about 5:1 to about 10:1.

The hydrogen peroxide used can vary in purity from 50 99.9~. The amount of hydrogen peroxide used must be in excess of the anhydride. Preferably, the molar ratio of hydrogen peroxide to 15 anhydride will be at least 2:1, and, most preferably, about 4:1.

The reaction conditions under which the process takes place include agitation of the mixture and heating. An example of this is a refluxing reaction, wherein temperatures of preferably about 35 to 45C, most preferably about 42C, for about 3 to 4 20 hours, are used, i~ methylene chloride is the immiscible solvent.

The end product, CYor~ alkyl monoperoxysuccinic acid is obtained by removing all solvent, e.q., by air drying, vacuum drying under reduced pressure, etc. Alternatively, recrystallization techniques could be used, such as shown in A.
25 Ault, Techniques and Experiments for Organic Chemistry, 2d Ed., pages 19-28, 1976, ~ ~5?6fi ~

For purposes of further exemplification, although the applicant does not intend to be solely qimited thereto, the method of preparing the novel compositions of this invention are illustrated below in EXPERIMENTAL.

EXPERIMENTAL

Example I
Synthesis of CY or ~ -Dodecyl Monoperoxysuccinic Acid CH3-(CH2)1 ~ C-o-OH
~ HC-I-O~

0.480ml 70~ hydrogen peroxide (lOm moles) and 4ml anhydrous 10 ethanol is placed in a 3-necked lOOml round-bottomed flask fitted with a reflux condenser, a mechanical stirrer, and a 50ml dropping funnel. The flask is surrounded by a water bath. The bath temperature is maintained at around 60 C. After the mixture has been vigorously stirred for 2 minutes, a solution of 1.34g ~5.0m 15 moles) of dodecyl succinic anhydride (Humphrey Chemical Co., recrystallized from hexane, m.p. 73-74C) in 20ml methylenechloride is added from the dropping funnel at such a rate that a moderate reflux is maintained. After the addition has been completed, an additional 0.480ml 70~ hydrogen peroxide is added in 20 one portion and the mixture is refluxed with continuous vigorous stirring for an additional 3.5 hours. The reaction mixture is then transferred to a 70 X 5mm crystallizing dish. The solvents are removed by evaporating in a hood. After being air-dried overnight, a yield of 1.5g of product, which is about 99~ with 25 respect to starting materials/ is obtained. Alternatively, product may be obtained by removlng solvent under reduced pressure 5~
and vacuum drying. A standard potassium iodide-thiosulfate titration, performed as shown in S.N. Lewis, ~Peracid and Peroxide Oxidations,~ in Oxidation, ~!ol. 1, pp 221-22 (1969), showed 3.42% (5.03~
5 theoretical) active oxygen. The structure of this product was assigned as a mixture of CYand ~ - octyl monoperoxysuccinic acid on the basis of the following spectral data: I~ (Nujol mull) 1750 cm , 1710 cm , C-N~IR (CD2C12, 90~HZ), ~-isomer, PPM, 176.0, 177.3, 14-91 (C-aliphatic); ~-isomer, PPM, 172.9, 180.3, 10 14-41 (C-aliphatic).

Example II

Synthesis of CY or ~-Octyl mono~ y~cc]~ ic acid 1l CH3-(CH2)7 ~ -C-O-OH
H HC-C-OH

O

CYor ~-octyl monoperoxysuccinic acid may be prepared according 15 to the procedure of Example I, above. In place of the dodecyl succinic anhydride (5 m moles), octyl succinic anhydride (5 m moles) is used. The yield for the reaction product, as calculated from the available oxygen, is 50~, using a standard potassium iodide-thiosulfate titration as in Example I, a~ove.

Example III

Synthesis of CY or ~ -Decyl monoperoxysuccinic acid ~0 CH3-(CH2)9 ~ -C-O-OH

H - HC-C-OH

CY or ~ -decyl monoperoxysuccinic acid may be prepared according to the procedure in Example I, above, by substituting decyl succinic anhydride (5 m moles) for the dodecyl succinic anhydride (5 m moles). Utilizing this procedure, the yield was 5 52% as calculated from the available oxygen, as shown in Examples I and II.

The preceding procedures have been successfully scaled up using larger amounts of the selected anhydride.

The applicants believe the procedures utilized are responsible 10 for the high yields of peroxyacids produced.

The above procedure comprises a safe, rapid and efficient process in which good yields of the desired CY or~ alkyl monoperoxysuccinic acids are obtained. Advantages of the present invention are that the reaction is performed in a rapid, safe and 15 easily controlled operation. The high heats of reaction, and expensive materials which were utilized in previous methods are avoided. As shown in the next section of the instant application, these alkyl monoperoxysuccinic acids are suitable for use as bleaching compositions.

2~ BLEACHING COMPOSITIONS

For fabric, textile or even hard surface bleaching purposes, at least 1 part per million active oxygen (p.p.m. A.O.) in the wash water or 1~ by weight of the surface active peroxyacid itself in the composition should be present. The range of the amount of 25 peroxyacid in solution should be about 1 to 30 p.p.m. A.O., or 1 à~3 to 30% by weight of the compositlon. Preferably, the amount of peroxyacid is about 5 to 2D% by weight of the composition.

Additionally, however, the surface active peroxyacids of the invention can be combined with various cleaning adjuncts, to form 5 bleaching compositions. One particular example is a bleaching composition comprising:

(a) A peroxyacid of the general structure R ~ - C - O - OH
H HC - C - OH
Il .

wherein R is a substituted or unsuhstituted straight chain 10 alkyl of 6 to 16 carbon atoms, substituted or unsubstituted branched chain alkyl of 6 to 20 carbon atoms, or a phenyl group which is substituted with one or more of H, alkyl of l to 14 carbon atoms, F, Cl, NO3, OSO3M, SO3M, or COOM, and wherein M is further defined as H, an alkali metal or ammonium cation; and tb) a stabilizer selected from:

hydrated aluminum salts, hydrated magnesium salts, carboxylic acids and boric acid.

Examples of these particular stabilizers can include potassium aluminum sulfate dodecahydrate, magnesium sulfate heptahydrate, 20 sodium aluminum sulfate dodecahydrate, magnesium ammonium sulfate hexahydrate, etc. Particular acid stabilizers besides boric acid include maleic acid, succinic acid, substituted-succinic acids, azelaic acid, dodecanedioic acid, cyclohexane dicarboxylic acid.

~5~
However, boric acid is particularly preferred as a stabilizer to prevent violent exothermic decomposition of this particular composition.

These particular ble~chin~ compositions may also comprise a filler selected from alkali metal and ammonium salts of sulfates, for example, sodium sulfate, ammonium sulfate and potassium sulfate. Other fillers are the alkali metal and ammonium salts of carbonates, bicarbonates, acetates and silicates. These fillers have the purposes of ~bulking~ the product to provide a 19 composition which is easily measured by the consumer.

Further, a builder may be added which can be selected from the alkali metal salts of carbonates, borates, polyphosphates, phosphates, zeolites, silicates; nitrilotriacetic acid and its alkali metal salts; and ethylene diamine tetraacetic acid and its 15 alkali metal salts. Particularly preferred as builders are such compounds as sodium carbonate, sodium tripolyphosphate, and nitrilotriacetic acid (NTA).

Also, particular laundry bleaching composition additives include surfactants selected fro~ anionic, nonionic, amphoteric, 20 cationic, and zwitterionic surfactants.

Anionic surfactants suitable for use in this invention include the alkali metal and ammonium salts of fatty acids, having about 8-20 carbon atoms in their chain lengths; substituted and unsubstituted alkyl sulfates; substituted and unsubstituted alkyl 25 sulfonates; substituted and unsubstituted alkyl benzene sulfonates (examples of which include both ~LAS~, for alkyl benzene sulfonic acid, and ~LAS~, for linear alkyl benzene sulfonate, sodium salt).

Still other suitable anionic surfactants include anionic aminocarboxylates, such as N-acyl-sarcosinatest alkyl, aryl, and alkylaryl sarcosinates; alpha-olefin sulfonates; sulfates of natural fats and oils (eg., castor, coconut, tallow oils);
sulfated esters; ethoxylated and sulfated alkylphenols;
ethoxylated and sulfated alcohols (also known as alkyl ether sulfates) and phosphated esters which are generally phosphorylated nonionics such as ethoxylated alcohols, ethoxylated alkylphenols, and polyoxythylene-polyoxypropylene block co-polymers.

Suitable nonionic surfactants include polyoxyethylenes, polyoxypropylenes; alkylpolyoxyethylenes;
alkylarylpolyoxyethylenes; ethoxylated alkylphenols; carboxylic acid esters such as glycerol esters of fatty acids, certain polyethylene glycol esters, anhydrosorbitol esters, ethoxylated 15 anhydrosorbital esters, ethylene and methylene glycol esters, propanediol esters, and ethoxylated natural fats and oils (eg., tallow oils, coco oils, etc.); carboxylic amides such as 1:1 amine acid diethanolamine condensates, 2:1 amine~acid diethanolamide condensates, and monoalkanolamine condensates such as ethanolamine 20 condensates, and isopropanol-amine condensates, polyoxyethylene fatty acid amides; certain polyalkylene oxide block co-polymers such as polyoxypropylene-polyoxyethylene block co-polymers; and other miscellaneous nonionic surfactants such as organosilicones.

Suitable cationic surfactants include a wide range of classes 25 f compounds, including non-oxygen-containing alkyl mono-, di- and polyamines, and resin derived amines; substituted alkyl, alkylol imidazolines, such as 2-alkyl-1-(hydroxyethyl)-2- imidazolines;
amide linked amines, and quaternary ammonium salts (~quats~

Further, suitable amphoteric surfactants containing both 30 acidic and basic hydrophilic moieties in their structuret include ~L2'~5~i6~

oxygen-containing amines, such as amine oxides (which appear to act as cationics in acidic solutions, and as nonionics in neutral or alkaline solutions); polyoxyethylene'alkyl and alicyclie amines; alkyl betaines, amino-carboxylic acids and salts thereof, 5 amino-carboxylic acid esters, and others.

Further examples of anionic, nonionic, cationic and amphoteric surfactants which may be suitable for use in this invention are depicted in Kirk-Othmer, Encyclopedia of Chemical Technoloqy, Third Edition, Vol. 22, pages 347-387, and ~cCutcheon's Detergents l0 and Emulsifiers, North American Edition, 1983;

zwitterionic surfactants whieh may be suitable ~or use in the compositions of this invention may be broadly described as derivatives of secondary and tertiary amines, derivatives of 15 heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternar~ phosphonium or tertiary sulfonium compounds. Suitable examples of these zwitterionic surfactants can be found described in Jones, U.S. 4,005,029, Columns 11-15;

The partieular surface aetive peroxyacid bleaches provided in this invention have been found to be particularly effective against various stains. For example, comparison of TABLE I below shows the following:
TABLE I
WAS~i WATER COMPOSITIONS ~ SRE1 GRASS

Tide ~ 2 B7.58 Octyl MPSA~ 20ppm A.O. 91.60 ~ecyl ~IPSA4 20ppm A.O. 93.44 Dodecyl MPSA5 20ppm A.O. 94.79 % SRE Grass. this is the percent stain removal of grass stains as measured spectrophotometrically. Higher values indieate better performance.

~5~
2 Tide ~ o is a registered trademark of Procter & Gamble Co.
for laundry detergent. 1.5 grams/l was present in all examples shown in this Table.

3 octyl ~PSA: this is an CYor ~ rnonoperoxysuccinic acid having 8 carbons in the alkyl chain.

4 Decyl MPSA: this is an CYor ~ monoperoxysuccinic acid having 10 carbons in the alkyl chain.
Dodecyl MPSA: this is an CY or~ monoperoxysuccinic acid having 12 carbons in the alkyl chain.

Further advantages of these peroxyacids are their relative stability in aqueous solution near their pKa's. It is generally agreed that for peroxyacids, pKa's are around 8.5-9.5. Within this range, optimal bleaching is obtained. Since most American washing machines and laundries operate at pH's of around 8-10, 15 this is also the particular range for favorable peroxyacid usage.
However, the benefit of obtaining the optimal activity of surface active peroxyacids at these particular p~'s also has the disadvantage of decreasing their stability.

' Surprisingly, however, the alkyl monoperoxysuccinic acids have 20 increased stability in aqueous solution at the optimal pH's.
Alkyl monoperoxysuccinic acids were dissolved in water, compared against somewhat silimar compositions, namely, alkyl butane diperoxoic acids, and found to have greater stability than these alkyl butane diperoxoic acids. These are shown in the three 25 illustrations, Figs. 1-3. Fig. 1 compares the octyl monoperoxysuccinic acid vs. the octyl butane diperoxoic acid.
Fig. 2 compares the decyl monoperoxysuccinic acid vs. the decyl butane diperoxoic acid. Fig. 3 compares the dodecyl monoperoxysuccinic acid vs. dodecyl butane diperoxoic acid. All 30 of these trials were run in a buffered solution at a p~ ranye of 8.3 - 9.0 at about 100F ~37.7 C), without additional water hardness, and with a surfactant, or a mixture of surfactants such as is found in Tide~ laundry detergent (registered trademark of Procter & Gamble) which includes a mixture of sodium alkyl sulfate, sodium alkyl ether sulfate, an'd sodium alkyl benzene sulfonate. Comparison of these figures shows that the alkyl

5 monoperoxysuccinic acids have much greater stability and longer half lives than the corresponding alkyl butane diperoxoic acids.

The foregoing examples and embodiments are solely for the purposes of illustration and not intended to restrict in any manner the scope of this invention. The invention is further 10 disclosed and illustrated by reference to the claims hereto.

Claims

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A process for synthesizing the monoperoxyacid having the general structure:

wherein R is an unsubstituted or substituted straight chain alkyl of 6 to 16 carbon atoms, unsubstituted or substituted branched chain alkyl of 6 to 20 carbon atoms, or a phenyl group substituted with one or more of H, alkyl of 1 to 14 carbon atoms, F, Cl, NO3, OSO3M, or COOM, in which the substitution, if any, is with one or more substituents H, alkyl of 1 to 14 carbon atoms, F, Cl, NO3, OSO3M or COOM, and M is further defined as H, an alkali metal or ammonium cation, said process comprising:
(a) combining:
(i) an alkylsuccinic anhydride of the general structure:

wherein R is defined as above;
(ii) a water immiscible organic solvent;
(iii) a water soluble organic solvent, said water immiscible organic solvent being in a ratio with said water soluble organic solvent of at least 2:1; and - Page one of Claims -(iv) hydrogen peroxide, said hydrogen peroxide being in a ratio with said anhydride in a ratio of at least 2:1;
and (b) agitating under heat; said process producing substantially no diperoxy acid.

2. The process of claim 1 wherein neither said water immiscible solvent nor said water soluble solvent reacts with either hydrogen peroxide or peroxyacid.

3. The process of claim 2 wherein the water immiscible solvent is selected from:
chlorinated, fluorinated or chlorofluorinated alkyls of 1 to 5 carbon atoms; and unsubstituted or halogenated aromatic hydrocarbons of 6-12 carbon atoms.

4. The process of claim 3 wherein said water soluble organic solvent is selected from:
straight chain, branched chain and substituted alcohols of 1 to 6 carbon atoms; straight chain, branched chain and substituted glycols of 1 to 6 carbon atoms, straight chain, branched and substituted glyeol ethers of 1 to 6 carbon atoms;
esters of 1 to 10 carbon atoms; ketones of 1 to 6 carbon atoms;
dioxane; acetonitrile; dimethyl formamide; and tetrahydrofuran, in which the substitution, if any, is with one or more substituents H, alkyl of 1 to 14 carbon atoms, F, Cl, NO3, OSO3M, or COOM, and M is further defined as H, an alkali metal or ammonium cation.

- Page two of Claims -

5. The process of claim 3 wherein said water immiscible solvent is methylene chloride.

6. The process of claim 5 wherein said water soluble solvent is a straight chain alcohol of 1 to 6 carbon atoms.

7. The process of claim 6 wherein the ratio of alcohol to methylene chloride is about 1:10.

8. The process of claim 7 wherein the amount of hydrogen peroxide must exceed the amount of anhydride in a molar ratio of at least 2:1.

9. The process of claim 8 wherein step (b) comprises a refluxing reaction.

10. The process of claim 1 further comprising (c) removing said solvents.

11. A process for synthesizing the monoperoxyacid wherein R is an unsubstituted or substituted straight chain alkyl of 6 to 16 carbon atoms, substituted or unsubstituted branched chain alkyl of 6 to 20 carbon atoms, or a phenyl group substituted with one or more of H, alkyl 1 to 14 carbon atoms, F, Cl, NO3, - Page three of Claims -metal or ammonium cation, in which the substitution, if any, is with one or more substituents H, alkyl of 1 to 14 carbon atoms, F, Cl, NO3, OSO3M or COOM, and M is further defined as H, or alkali metal or ammonium cation, the process comprising:
(a) combining:
(i) an alkyl-substituted succinic anhydride wherein R is as defined as above;
(ii) a water immiscible organic solvent;
(iii) hydrogen peroxide; and (iv) a water soluble organic solvent to carry the hydrogen peroxide into solution; and (b) refluxing the combination;
said water immiscible organic solvent and said water soluble organic solvent being in a ratio of at least 2:1; said hydrogen peroxide and said anhydride being in a ratio of at least 2:1; and said process producing substantially no diperoxy acid.

12. The process of claim 11 wherein the compound synthesized has the structure:

the process comprising (a) combining:
(i) an alkyl-substituted succinic anhydride wherein R is as defined as above;
(ii) a water immiscible organic solvent;
- Page four of Claims -(iii) hydrogen peroxide; and (iv) a water soluble organic solvent to carry the hydrogen peroxide into solution; and (b) refluxing the combination;
said water immiscible organic solvent and said water soluble organic solvent being in a ratio of at least 2:1; said hydrogen peroxide and said anhydride being in a ratio of at least 2:1; and said process producing substantially no diperoxy acid.

13. The process of claim 11 wherein the compound synthesized has the structure:

the process comprising (a) combining:
(i) an alkyl-substituted succinic anhydride wherein R is as defined as above;
(ii) a water immiscible organic solvent;
(iii) hydrogen peroxide; and (iv) a water soluble organic solvent to carry the hydrogen peroxide into solution; and (b) refluxing the combination;
- Page five of Claims -said water immiscible organic solvent and said water soluble organic solvent being in a ratio of at least 2:1; said hydrogen peroxide and said anhydride being in a ratio of at least 2:1; and said process producing substantially no diperoxy acid.

14. The process of claim 11 wherein the compound synthesized has the structure:

the process comprising (a) combining:
(i) an alkyl-substituted succinic anhydride wherein R is as defined as above;
(ii) a water immiscible organic solvent;
(iii) hydrogen peroxide; and (iv) a water soluble organic solvent to carry the hydrogen peroxide into solution; and (b) refluxing the combination;
said water immiscible organic solvent and said water soluble organic solvent being in a ratio of at least 2:1; said hydrogen peroxide and said anhydride being in a ratio of at least 2:1; and said process producing substantially no diperoxy acid.

- Page six of Claims -